


That One Time in Delaware

by antarshakes



Category: Supernatural
Genre: Alternate Universe, Dean still is, Dean was a twink, M/M, Oh Dean, Plot What Plot/Porn Without Plot, Prostitute Dean, Prostitution, Robo!Sam is a scary fucker, The 90s, Time Travel, Top!Sam, Underage - Freeform, Underage!Dean, Why does Cas do the things he does?, Wincest - Freeform, robo!sam
Language: English
Status: Completed
Published: 2012-11-24
Updated: 2012-11-24
Packaged: 2017-11-19 10:49:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 3,727
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/572455
Author URL: https://archiveofourown.org/users/antarshakes/pseuds/antarshakes
Summary: <blockquote class="userstuff">
              <p>Cas hides Robo!Sam in the 90's, where he meets the younger version of Dean, sixteen years old and hooking to be able to survive the next day.</p>
            </blockquote>





	That One Time in Delaware

**Author's Note:**

> written for the blindfold_spn kink meme, where anon asked for: RoboSam goes time travelling for some reason and ends up back in the ‘90s. Either intentionally or accidentally, he finds a younger Dean (no younger than 16 please) selling himself on the street to get money for he and ‘90s Sam’s survival. RoboSam figures ‘why not’ and takes Dean back to a motel room to fuck him.
> 
> p.s.  
> Even though this was looked over by the amazing [Maichan](http://maichan808.tumblr.com/), I tinkered around with it A LOT, so all remaining mistakes are mine (and feel free to point them out to me! I appreciate that shit)

*-*-*

With one tap against his noggin, Sam is dropped unceremoniously into a random bathroom stall in a random mall in the middle of Bumfuck, Nowhere.

He kicks open the stall door, scaring the one guy into pissing on his own shoes as he gives Sam a frightened look.

Sam first notes the man’s tracksuit and a Walkman hanging off his belt, before he pins the guy with another look. “Hey guy, where the hell am I?”

The guy stutters out a “Dover,” and hurriedly zips up his pants.

“Dover, Delaware?” Sam asks. The guy nods, wipes his hands off on his pants and speed walks out of the bathroom. Sam calmly saunters out after him, listening to the guy's swish-swish, suspecting he’s in the 90s, in fucking Delaware.

He makes his way through the throng of people to the nearest exit, looking left and right, before opting for right.

Sam, of course, remembers Dover. They spent some time here. Might have even been a few months. Cas has apparently dropped him off in the 90's, with no explanation whatsoever. And if it weren’t for the inconvenience of not having his gear at hand, Sam wouldn’t give two shits about getting the fuck out of here.

He stalks his way to the outskirts of town, where the people aren’t so much in a hurry, judging from the folks leaning against lampposts and lurking in doorways. Sam thinks he might remember this neighborhood and when he spots a familiar old motel, he’s sure: this is where they were staying.

Sam’s about to make his way over, when he spots a kid stumbling out of a car in front of the entrance. The kid smirks while he straightens his jacket and wipes a hand across his mouth. When he turns his head, Sam gets a good look at his face. A grin involuntarily breaks out over his own features. That’s his brother right there. Dean can’t be older than sixteen and his younger self can’t be too far away. The memories come flooding back now. They were stashed in that seedy motel for two months while their Dad was supposed to do a two-week job. Just him and Dean stinking up the room like crazy. Sam remembers spending hours in their room, reading books that Dean would bring in and take away as soon as he was done with them.

Sam looks on, bemused, and lets out a “huh,” when Dean doesn’t immediately return to the motel, but instead crosses the street and chooses a spot near some mailboxes across from a convenience store. Sam looks on as Dean cocks one hip and keeps his hand resting lightly on his pocket, no doubt keeping his earnings safe. It doesn’t take long for someone to step up to Dean, exchange a few words, and lead him into a dark alleyway.

Sam, out of boredom or curiosity, whatever you want to call it, crosses the street and follows the path Dean had taken. He makes sure to stay in the shadows as he watches how Dean drops to his knees and takes a random cock in his mouth, going to town like there’s no tomorrow. The guy he’s blowing is a middle-aged man, pudgy, and Sam finds it miraculous that Dean was even able to find his cock. The guy keeps blabbing about how Dean’s a “good little bitch, ain’t ya?”. It’s frankly pathetic to watch how he loses it in less than five minutes. Dean spits out the man’s come onto the ground, stands up again, and tucks the guy in. The john tries to catch his breath, while digging around for some bills. He stuffs them in Dean’s pocket and slaps Dean’s ass as he walks away. With one last grin thrown over his shoulder, Dean makes his way out of the alley.

Sam remembers Dean being gone for hours on end, but he’d be home every evening, making sure Sam would get to bed on time. Sam also remembers waking up in the middle of night to see Dean’s bed empty, or hear the shower running, or the sounds of retching coming from the bathroom. Well, Sam thinks, guess this is what old Dean-o was doing. He should’ve known that Dad didn’t think to leave them more money than the two weeks he was supposed to be gone required. If only John Winchester knew what his son was really up to.

Sam makes his way to their motel, remembers the floor they were on, and requests the same. He figures he might as well stick around something he knows. Sam and the old them are the only ones on that floor. 

That same night Sam hears arguing and recognizes his own childish voice, telling Dean that he’s, ‘not Dad’ and  _why_  does he leave Sam alone all the time.  _Why_  doesn’t Dean want to spend time with him?

Dean’s weary voice cuts through, telling younger Sam that he needs space to himself from time to time and doesn’t like being cooped up, especially since he doesn’t have the patience to finish books like Sam does.

By then Sam has stepped out of his motel room, leaning against the wall near his door. He can make out their words perfectly from here. Not too long after the voices have died down, does Dean himself step outside, closing the door behind him softly. As if he senses Sam, he looks up sharply.

Sam used to think Dean was bigger than life back then. Nothing could hurt his loudmouth brother and Dean was king of the world. All Sam wanted to do back then was wipe that fucking permanent smirk off of Dean’s face, make a dent in his bravado. Looking at his sixteen-year-old brother now, Sam sees no traces of that. He sees a scared, clueless kid and instead of feeling remorse about treating his brother like that back then, he wants to explore this kid further.

Sam licks his lips and Dean seems frozen on the spot. He recovers quickly though, glancing back towards the door as if silently willing younger Sam to lock the bolt. He looks back towards Sam and Sam can tell that he slipped his game-face on in that split second.

“Can I help you?” he asks in a voice that’s a few octaves lower than his usual. When Sam just raises an eyebrow, Dean walks past him towards the elevator.

From the elevator, Dean cuts him another puzzled look. Sam wonders if Dean recognizes him and sees the vestiges of pudgy little Sam in his face. He stares Dean down, until Dean turns away with a high blush on his cheeks, shoulders visibly tense.  Sam enjoys toying with Dean like this… as much as he can enjoy anything, that is.  
  
“Hey, kid,” he calls out.

When Dean looks back, he jerks his head towards his own door. That seems to be the last straw for Dean and he stalks over. “Look man, I don’t know what you take me for but–” Before he can get the rest of the sentence out, Sam grabs Dean in a move that he knows Dean hasn’t learned to block yet and has him right against the wall. 

“You’re selling,” Sam breathes into Dean’s shocked face, “I’m buying.”

Dean struggles momentarily, but seems to give up when he can’t get out of it. He chances another glance at his own room door and back to Sam. “Fine. But no kinky shit.”

With that, Sam releases him and pushes Dean inside his room.

“What’s the going rate, kid?”

“Fifty for a blowjob, a hundred for fucking. I don’t spend the night and I’m not calling you Daddy,” Dean delivers with a smirk.

Sam has to laugh at that, because the humor in this situation is not lost on him. Dean has a small smile playing on his lips when Sam stops laughing.

“You sure we haven’t met, man? You look awful familiar.”

Sam smirks at that. “Nah, kiddo. I’m sure you would’ve remembered me.”

Dean stares at him for a few beats longer and gives a small nod. “So what’s it gonna be?”

Sam takes his time settling on the bed. “What’s the rush?” he asks. “How about, you take your clothes off first, and then let me decide how to use you before I pay you double’s worth, hm?”

Dean sucks in a breath and nods, keeping an eye on Sam as he undresses. The first thing he takes off is the pendant Sam gave him all those years ago, the same way Sam has seen him do ever since he got that little trinket. Dean stuffs it in his pocket, before he removes his jacket followed by his shirt. Dean’s body is pale and freckled, he’s still soft and boyish with a hint of a six pack trying to show. He’s going to get bulkier in ten/fifteen years, but for now, he’s still a twink with features just this side of feminine and way too pretty for a boy his age. Dean starts on his boots next, then socks, pants, and finally his briefs. His body is smooth, not a hair in sight.

“What’s your name kid?” Sam asks, wanting to know what alias Dean would use for his Pretty Woman persona.

“Dean,” he answers after a few beats, and then, “yours?”

Sam contemplates lying, but for some reason he wants to mess with Dean’s mind.

 “Sam.”

Dean looks him up and down in appraisal. “You look like a Sam.”

“You look like Julia Roberts, now undress me.”

Dean visibly bristles at that, but like the true, little prostitute he is, he doesn’t say anything about it. He saunters over to where Sam’s sitting on the bed and straddles Sam’s lap. The weight of him on Sam is nothing, just a small, skinny thing adding some pressure. If he wanted to, he could fling him across the room with no effort at all. He should find this funny, because as much as Dean loves to use his looks, he has desperately tried to get away from them too. He knows Dean started to eat more and exercise more rigorously when Sam started to outbulk him. If only he could see the stark difference between his twinky self and what Sam has grown in to.

Dean’s still-soft hands start unbuttoning Sam’s shirt from bottom to top, nothing like the coarseness Dean has now, fingers crooked and calloused from years in the life.

 Dean wiggles on Sam’s lap as he slides the shirt off Sam’s shoulders, caressing his hands over Sam’s muscles. Sam feels himself start to harden from the stimulation, but it’s nowhere close to getting where he’s planning on going. Once his shirt is fully vested, Sam lifts Dean off his lap and drops him unceremoniously on the bed. That all-too-familiar indignant look comes back to Dean’s face, but he doesn’t say a word.

“Take my cock out,” Sam orders, “and get me hard.”

Dean complies immediately and starts unbuttoning Sam’s pants, lowering Sam’s underwear just enough so he can get Sam’s dick free. Dean’s eyes widen at the sight, no doubt wondering how he’s going to take it, but again, he remains quiet. He starts by jacking Sam slowly, putting his mouth on Sam’s half-hard dick, until he’s so stiff Dean can’t swallow his entire length.

“You can take it all, can’t you Dean-o?” Dean’s head perks up slightly at his childhood nickname, but he just nods, relaxing his throat to let Sam all the way in. His tongue works slowly up and down the ridges and the vein. Sam wonders how many cocks Dean has had in his mouth to be able to take him like this. He shoves forward a little bit to see if he can get a reaction out of Dean. Dean chokes a little bit, but he doesn’t let anything on, just keeps bobbing his head up and down, jacking Sam faster.

If Dean thinks this is all there’s going to be, he has another thing coming. Sam forcefully lifts Dean’s mouth from his cock, making a string of saliva stick to Dean’s puffed up lips. He rubs his dick over Dean’s lips for good measure and then pushes him backwards.

“Ass up in the air, kid.”  When Dean just looks at him, Sam rolls his eyes. “I got condoms, boy scout. Don’t worry about it.”

Dean licks his lips and turns over, head leaning on his hands as he raises his ass up as high as it can go. His balls hang heavy between his legs and Sam idly admires that his brother is such a good cockslut. Noticing his smooth hole, Sam rubs the pad of his thumb over it, easily slipping it inside.

“Still so loose, boy scout,” Sam notes absently. “How many cocks did you take today?”

“Enough to take you,” he hears Dean mutter.

“Oh really?” Sam asks. “Enough to take a fist as well?” Dean’s asshole clenches hard at that, prompting Sam to laugh and bend over to lick at his rim. When he pushes his whole thumb inside, Dean just shudders. He reaches out his other hand, seeking out Dean’s mouth with three fingers.  
  
“Get ‘em good and wet, Dean. It’s all you’re going to get.” At that, Dean starts sucking on Sam’s fingers with more vigor. Keeping his right hand in Dean’s mouth, he licks around Dean’s hole, fucking his left thumb in and out. No matter what, dry fucking is fun for no one. On the moan around his fingers, Sam pulls out and slowly stuffs the three wet digits into Dean’s glistening hole, one by one. There’s still some resistance, but Dean’s pushing back, and Sam doesn’t really care either way.

“Fuck yourself loose on them,” Sam orders. His jeans are still mid-thigh on him, but not really restricting him, so he doesn’t bother taking them all the way off. He roots around in his pocket for a stray condom and rips the packet open with his teeth. Sam pulls his fingers out just as Dean seems to be getting really into it. Dean watches him with dark eyes from beneath his lashes, watching and making sure the condom is on right and is secured. Sam just gives him a bemused look back as he tugs at the tip of the condom, spits on his hand, lubes up his cock and sits down on the edge of the bed. With another look thrown over at Dean behind him, he gestures at his dick: “Ride it, kid.”

Dean’s arms are shaking when he moves off the bed and plants his knees on both sides of Sam’s hips, slowly lowering himself onto Sam. The head of Sam’s dick breaches Dean’s hole easily, but it’s the girth that Dean seems to have trouble with taking. So Sam wraps a steadying arm around Dean’s narrow waist and shallowly fucks in and out of him before thrusting all the way in with a grunt. Dean matches him with a loud groan, muttering “shit, shit, shit,” as Sam orders him to move. On trembling legs, Dean lifts himself up and on the downward stroke, Sam thrusts upwards, making Dean cry out.

“Christ, Dean-o. Makes me think you’ve never had a real cock up there.”

Sam takes a good look at Dean’s face: sweat beading on his brow, eyes shut tight, lips gnawed puffy, and body fully flush. Sam stills his movements, causing Dean to open his eyes and hold Sam’s gaze.

Then Dean lurches forward and catches Sam’s mouth using those same lips Sam has seen on countless of chicks. Too startled to protest, Sam lets him play with his tongue for a bit, before resuming his thrusting. Dean groans around his tongue as he starts pushing back, trying to bounce up and down, but unable to settle on a rhythm.

The push and pull gets tiresome pretty quick and Sam pulls out, manhandling him onto the bed again.

“I think you’re worth more ass up, kid.”  
  
He slaps Dean’s ass to get him scrambling quickly into position. When Sam enters him again, he just drops his head on the bed, fisting the sheets. Sam takes a moment to look at the way he has Dean lithe body speared on his cock; his flushed red cock stands out starkly against the pale skin of Dean’s ass cheeks, asshole spread obscenely wide. Sam shoves forward a bit to see Dean’s hole widen further. He does that a couple of times, pulling out just to see Dean’s hole taking him over and over again, opening up so easily for him.

A groan from Dean pulls Sam from his reverie and with a snap of his hips, begins to fuck Dean in earnest. He knows Dean is loving it when on every stroke of his prostate, Dean bites into the cheap sheets. The slapping of skin on skin, balls on balls, resonates in the room along with Sam’s heavy breathing and Dean’s muffled, hoarse moans. It doesn’t take long before Dean is clamping down hard on Sam’s cock and spurting helplessly onto the sheets, his cock untouched.

Sam drags his hand through the mess on Dean’s stomach and pulls his cock out to cover it with come, before he pushes back in. The glide is ridiculously smooth, and with every thrust Dean’s hole gets more and more wet. He starts ruthlessly fucking into Dean, while Dean tries his best to fuck back. When Sam reaches for Dean’s spent cock, squeezing it, Dean lets out a high keen, clamping down hard on Sam. As he feels his balls draw up, he pulls out, ripping the condom off, and flipping Dean over on his back with the other.

“Open up, Dean-o,” he orders and Dean obligingly opens his mouth. Just a few pulls and Sam is spurting onto Dean’s neck, mouth and cheeks.

Dean licks up everything he can reach and lies there spent, chest heaving quickly. Wringing the last drops out his cock, Sam stands up and locks gazes with Dean. His moistened eyelashes are clumped together, and the green of his eyes have never been more vibrant. His hair sticks up in all kinds of ways and he looks truly like the whore he is.

Sam breaks the staring contest to bend down and reach for the pockets of the jeans still pooled around his ankles. He takes out every bill in there and tosses them onto the bed next to Dean, smirking when some of it lands in come. Dean’s eyes widen when he takes in the amount strewn around him. With that sum, he knows that Dean and his younger self can make it well to next month with some extra to spare.

“This earns you another round, y’know,” Dean adds quietly, voice shot.

“This is all I’m buying, now get dressed and gone, kid.” He knows Dean wants to take a shower, but Sam’s not giving him that, knowing that Dean will have to go back to his room, to younger Sam who will still be up, and Dean will have to explain himself. He doesn’t care

He takes off his shoes and pants as he waits for Dean to gather his stuff and get going. When Dean’s all ready, pocket bulging with the cash Sam gave him, Sam lets Dean have a good look at him. He smiles at Dean, baring his teeth as he points to himself and to the room around them, “be sure to remember this, Dean-o.”

Dean gives him a puzzled look before he disappears, softly closing the door behind him.

Sam stands in the room a bit longer, eyeing the dirty sheets. He scratches idly at his pubes and kicks his shoes away, making his way to the shower. He cleans himself, perfunctory, and returns to his room, absently wondering how he’s going to get back to the future, when there’s a knock on the door. Not bothering with anything to cover himself with, he opens the door to find his younger self standing on the other side – short and soft, with big eyes and too much hair.  
Young Sam is blushing beet red under the scrutiny, but Sam can see the determination on the boy’s face.

Holding out a small fist with a wad of cash in it, he blurts out, “we ain’t taking your money, mister.”

Sam laughs scoffingly in his face. “Of course you’re not.”

He’s about to shut the door, but his younger self worms his way in to the room, throwing the money on the ground.

“Like I said,” Young Sam continues, thrusting his pointy chin up in defiance, "we ain’t taking this kinda money.”

“Oh, Sammy,” he replies, relishing how his younger self physically recoils. Sam kicks the money on the floor out the door as his younger self watches on with wide eyes.

“I don’t care if you take the money or not. Dean earned it being a good whore.” Anger and hurt war with one another on Sammy’s face with every word he hears. “You can either let the money go to some lowlife in this motel, or you can take it, pretend you don’t know where it comes from so Dean doesn’t have to whore himself every night to feed you for the next month. You choose.”

Sam watches as the pride in his younger self disappears with every word Sam tosses out. When he’s done, the boy bends down in resignation and slowly gathers every single bill. When he’s finished, he stands up again and looks at Sam, studying him. He is still stark naked, and Sammy eyes him from head to toe.

Winking at his younger self, he adds: “It’s okay to look, Sammy. This is your future in say… fifteen years anyway.” When the boy just gapes at him in astonishment, Sam growls out a, “now scram.”

Sammy hurries away while Sam closes the door. Dragging his hand through his wet hair, he turns around preparing for a night of nothing when he spots Cas. Before he can get a word in, Cas grabs his arm with brute strength and he’s back to the present. He must be, because his older brother is there, color high on his cheeks as he draws his arm back and knocks Sam out.

\---

End

**Author's Note:**

> as always: I'm also on [Tumblr](http://antarshakes.tumblr.com/) squeeing about Stucky, Sterek or Wincest ;) Come say hi!


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